3-Isobutyl-1-methylxanthine (HCID 3758)

Names & identifiers

Preferred name: 3-Isobutyl-1-methylxanthine
IUPAC: 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
English name: 3-Isobutyl-1-methylxanthine
Molecular formula: C10H14N4O2
Molecular weight: 222.24

Names & synonyms

3-Isobutyl-1-methylxanthineIBMX28822-58-4isobutylmethylxanthine1-METHYL-3-ISOBUTYLXANTHINE1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-Xanthine, 3-isobutyl-1-methyl-3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione3-Isobutyl-1-methyxanthine3-isobutyl-1-methyl-7H-xanthine1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dioneSC-2964

Show more names

MIXIMXI5879-1GNSC 165960I5879-100MGI5879-250MGIBMX(NSC165960

TBT296U68MCHEBI:347951-methyl-3-(2-methylpropyl)-3,7-dihydro-1H-purine-2,6-dioneNSC-165960SC 2964DTXSID0040549Isobutyltheophylline3 Isobutyl 1 methylxanthine

Database identifiers

CAS: 28822-58-4
PubChem CID: 3758
DTXSID: DTXSID0040549
ChEMBL: CHEMBL275084
ChEBI: CHEBI:34795
UNII: TBT296U68M
EC Number: 249-259-3
Nikkaji: J107.263C

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 69.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 318

Experimental & physicochemical properties

Kovats Retention Index2150；2150；2150

Collision Cross Section147.8 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 200 · 200-201 °C(lit.)
Boiling point: 363.42 °C · 363.42°C (rough estimate)
Density: 1.2042 · 1.2042 (rough estimate)
refractive index: 1.65 · 1.6500 (estimate)
storage temp.: -20 °C · -20°C
solubility: 1 M · DMSO: 1 M with gentle warming
form: powder
pka: 8.61 · 8.61±0.70(Predicted)
color: off-white
BRN: 247859 · 247859
Stability: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI: InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
InChIKey: APIXJSLKIYYUKG-UHFFFAOYSA-N
SMILES: N1C2=C(N(CC(C)C)C(=O)N(C)C2=O)NC=1
CAS DataBase Reference: 28822 · 28822-58-4(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 296 U68M · TBT296U68M
UNSPSC Code: 12352202 · 12352202
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312a-P330-P501a
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
RTECS: 8500000 · ZD8500000
HS Code: 29335990 · 29335990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 2 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk: 3
rtecs: ZD8500000
hs_code: 29335990
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Precautionary statements: P264-P270-P301+P312a-P330-P501a

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationCompounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Applications · 5 items

DescriptionIBMX (28822-58-4) is a pan-specific inhibitor of phosphodiesterases (IC50=2-50 μM). Inhibition of PDEs leads to increased concentration of intracellular cAMP which activates PKA.2IBMX does not inhibit PDE8 or PDE9.3Weak adenosine receptor antagonist.4

UsesA nonspecific inhibitor of phosphodiesterases

Usesphosphodiesterase inhibitor

Uses3-Isobutyl-1-methylxanthine is used in inhibition of phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50 = 1.3 uM). Also inhibits ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Inhibits the growth of carcinoma cells both in vivo and in vitro in mice.

General Description3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

Additional notes

DefinitionChEBI: 3-isobutyl-1-methyl-9H-xanthine is a 3-isobutyl-1-methylxanthine. It is functionally related to a 9H-xanthine. It is a tautomer of a 3-isobutyl-1-methyl-7H-xanthine.